NP-MRD: Showing NP-Card for (3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0318562)

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Record Information

Version

2.0

Created at

2022-09-11 19:07:59 UTC

Updated at

2022-09-11 19:07:59 UTC

NP-MRD ID

NP0318562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one

Description

Zhepiresinol belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. (3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one is found in Peperomia heyneana. Based on a literature review very few articles have been published on zhepiresinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.7795   -3.4789    0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383   -2.2526    0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -1.0248    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.9239   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    0.2926   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    0.4434   -0.4107 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1359    1.5749    0.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4987    1.2885    0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.0900    0.9834 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5959   -0.9240    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4915   -1.1427    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -1.3879   -0.5513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1365   -1.4561   -0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453   -0.7310    0.1388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6097    1.4365   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    1.3882    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7349    2.5496    0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    3.8304    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420    0.1399    0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205    0.0807    0.5000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8263    0.0430   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -4.2700    0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891   -3.5180    0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -3.7581   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853   -1.8555   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    0.5775   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    2.0319    1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9380    1.1964   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216   -0.0444    2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -2.5350   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367   -1.0298   -1.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7327   -1.4351    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    2.3975   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.8657    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273    4.6078    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892    3.9965   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875    0.4455   -1.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7070    0.6700   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -0.9989   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 19  3  1  0
 14  6  1  0
 10  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
  6 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  1
 14 32  1  1
 13 30  1  0
 13 31  1  0
M  END


  Mrv1652309112221082D          

 21 23  0  0  1  0            999 V2000
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -3.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8018   -4.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)[C@H]1OC[C@H]2[C@@H]1COC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O6/c1-17-11-4-8(5-12(18-2)14(11)19-3)13-9-6-21-15(16)10(9)7-20-13/h4-5,9-10,13H,6-7H2,1-3H3/t9-,10-,13+/m0/s1

> <INCHI_KEY>
BYXOLWYJKZALLQ-OUJBWJOFSA-N

> <FORMULA>
C15H18O6

> <MOLECULAR_WEIGHT>
294.303

> <EXACT_MASS>
294.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.514624282491468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR)-4-(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-one

> <JCHEM_LOGP>
0.8545473266666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.99496337837656

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
73.12110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3H-furo[3,4-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.595  -5.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.775   2.235   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.479  -6.940   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.003  -8.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.942  -6.116   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.466  -7.580   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.497  -8.725   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    5   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    3   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₆

Average Mass

294.3030 Da

Monoisotopic Mass

294.11034 Da

IUPAC Name

(3aR,4S,6aR)-4-(3,4,5-trimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-one

Traditional Name

(3aR,4S,6aR)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3H-furo[3,4-c]furan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1OC[C@H]2[C@@H]1COC2=O

InChI Identifier

InChI=1S/C15H18O6/c1-17-11-4-8(5-12(18-2)14(11)19-3)13-9-6-21-15(16)10(9)7-20-13/h4-5,9-10,13H,6-7H2,1-3H3/t9-,10-,13+/m0/s1

InChI Key

BYXOLWYJKZALLQ-OUJBWJOFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Peperomia heyneana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Lignan lactone
Furanoid lignan
Furofuran lignan skeleton
Phenoxy compound
Methoxybenzene
Furofuran
Anisole
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.85	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.12 m³·mol⁻¹	ChemAxon
Polarizability	29.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040731

Chemspider ID

23281356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44421317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0318562)

MOL for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D MOL for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D SDF for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D-SDF for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

PDB for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D PDB for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

SMILES for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

INCHI for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

Structure for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D Structure for NP0318562 ((3ar,4s,6ar)-4-(3,4,5-trimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)